US5416125A - Process for the production of semirigid foams containing urethane groups with improved flow properties - Google Patents

Process for the production of semirigid foams containing urethane groups with improved flow properties Download PDF

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Publication number: US5416125A
Authority: US; United States
Prior art keywords: weight; mixture; diphenylmethane diisocyanate; polyisocyanates; production
Prior art date: 1993-10-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

US08/325,715

Other languages

English (en)

Inventor

Ulrich Liman

Peter Gansen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-10-29

Filing date

1994-10-19

Publication date

1995-05-16

1994-10-19 Application filed by Bayer AG filed Critical Bayer AG

1994-10-19 Assigned to BAYER AKTIENGESELLSCHAFT KONZERNVERWALTUNG RP reassignment BAYER AKTIENGESELLSCHAFT KONZERNVERWALTUNG RP ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: GANSEN, PETER, ULRICH, LIMAN

1995-05-16 Application granted granted Critical

1995-05-16 Publication of US5416125A publication Critical patent/US5416125A/en

2014-10-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 26
239000006260 foam Substances 0.000 title claims abstract description 19
238000004519 manufacturing process Methods 0.000 title claims abstract description 17
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 8
239000000203 mixture Substances 0.000 claims abstract description 42
229920001228 polyisocyanate Polymers 0.000 claims abstract description 23
239000005056 polyisocyanate Substances 0.000 claims abstract description 23
-1 polymethylene Polymers 0.000 claims abstract description 21
239000011541 reaction mixture Substances 0.000 claims abstract description 18
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims abstract description 17
229920006389 polyphenyl polymer Polymers 0.000 claims abstract description 11
LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims abstract description 10
150000002894 organic compounds Chemical class 0.000 claims abstract description 10
239000004604 Blowing Agent Substances 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 10
239000002985 plastic film Substances 0.000 claims description 7
229920006255 plastic film Polymers 0.000 claims description 7
239000000654 additive Substances 0.000 claims description 6
239000002131 composite material Substances 0.000 claims description 5
239000012948 isocyanate Substances 0.000 description 13
150000002513 isocyanates Chemical class 0.000 description 12
229920005862 polyol Polymers 0.000 description 8
150000003077 polyols Chemical class 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
229920000570 polyether Polymers 0.000 description 7
239000004721 Polyphenylene oxide Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 5
239000004814 polyurethane Substances 0.000 description 5
229920002635 polyurethane Polymers 0.000 description 5
239000004872 foam stabilizing agent Substances 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
229920005830 Polyurethane Foam Polymers 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
239000000463 material Substances 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
239000011496 polyurethane foam Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
239000003429 antifungal agent Substances 0.000 description 2
239000000022 bacteriostatic agent Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
239000006229 carbon black Substances 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
239000000975 dye Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000005187 foaming Methods 0.000 description 2
230000001408 fungistatic effect Effects 0.000 description 2
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000004014 plasticizer Substances 0.000 description 2
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
239000004800 polyvinyl chloride Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000276489 Merlangius merlangus Species 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920000265 Polyparaphenylene Polymers 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
238000007046 ethoxylation reaction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000011521 glass Substances 0.000 description 1
HJJLDNAELNDBBL-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO.OCCCCCCO HJJLDNAELNDBBL-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000000465 moulding Methods 0.000 description 1
CAAWLEUNKIZZLS-UHFFFAOYSA-N n,n-bis[3-(dimethylamino)propyl]formamide Chemical compound CN(C)CCCN(C=O)CCCN(C)C CAAWLEUNKIZZLS-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920005906 polyester polyol Polymers 0.000 description 1
229920002959 polymer blend Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical class NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
238000003856 thermoforming Methods 0.000 description 1
229920002397 thermoplastic olefin Polymers 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0016—Foam properties semi-rigid
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent

Definitions

This invention relates to a process for the production of semirigid foams containing urethane groups which exhibit very good flow properties during the foaming process. Due to the good flow properties of the reaction mixtures, these reaction mixtures are even capable of filling closed molds of complicated construction including, for example, molds of the type used in automobile manufacture for the production of back-foamed instrument panels, without any unwanted defects and voids.
German Offenlegungschrift 4,001,556 describes mixtures of tolylene diisocyanate and diphenylmethane diisocyanate as the polyisocyanate component for the production of flexible foams.
these flexible foams are unsuitable for the production of instrument panels because they do not show satisfactory flow properties in the production of semirigid polyurethane foams.
tolylene diisocyanate is often undesirable to processors for reasons of industrial hygiene.
reaction mixtures comprise special mixtures of diphenylmethane diisocyanate (MDI) and polyphenylene polymethylene polyisocyanate (PMDI).
MDI diphenylmethane diisocyanate
PMDI polyphenylene polymethylene polyisocyanate
MDI/PMDI mixtures differ from hitherto known mixtures in their relatively high content of monomeric MDI isocyanates, more particularly the 2,4'-MDI content.
Typical modifications of these isocyanates for example, by urethane, carbodiimide, isocyanurate or urea groups, lead to similar positive effects.
the present invention relates to a process for the production of semirigid foams containing urethane groups by reacting a reaction mixture comprising:
polyisocyanates comprise a mixture of
the reaction mixture may optionally comprise:
the polyisocyanate mixtures comprise:
plastic films are backfoamed with the foam-forming reaction mixture to form film/foam composites.
Suitable mixtures of isomers of diphenylmethane diisocyanate and polyphenyl polymethylene polyisocyanates comprise: a) 55 to 87% by weight, based on 100% by weight of the mixture, of 4,4'-diphenylmethane diisocyanate, b) 8 to 40% by weight, based on 100% by weight of the mixture, of 2,4'-diphenylmethane diisocyanate, c) 0.1 to 4% by weight, based on 100% by weight of the mixture, of 2,2'-diphenylmethane diisocyanate, and d) 5 to 35% by weight, based on 100% by weight of the mixture, of polyphenyl polymethylene polyisocyanates.
these mixtures comprise: a) 60 to 75% by weight of 4,4'-diphenylmethane diisocyanate, b) 10 to 25% by weight of 2,4'-diphenylmethane diisocyanate, c) 1 to 3% by weight of 2,2'-diphenylmethane diisocyanate, and d) 20 to 30% by weight of polyphenyl polymethylene polyisocyanates.
Modification products of these isocyanates which contain, for example, urethane, carbodiimide, isocyanurate or urea groups are also suitable for the present invention.
polyether and/or polyester polyols having a functionality of 2 to 4 and a molecular weight of 150 to 8,000 are suitable for the urethane modification (i.e. prepolymer formation).
suitable polyols include polypropylene glycols having molecular weights in this range.
the process also requires organic compounds containing at least two isocyanate-reactive hydrogen atoms and having a molecular weight of generally 400 to 10,000.
Suitable compounds include, for example, those compounds containing amino groups, thiol groups or carboxyl groups.
Compounds such as these preferably include, for example, compounds containing hydroxyl groups, preferably polyethers, polyesters, polycarbonates, polylactones and polyamides.
those containing 2 to 8 hydroxyl groups are preferred, with those having molecular weights in the range of 1,000 to 8,000 being more preferred, and those having molecular weights in the range of 2,000 to 4,000 being most preferred.
a particularly preferred embodiment is characterized by the use of polyether polyols which have been obtained by the alkoxylation of trifunctional starter molecules, more particularly trimethylol propane and/or glycerol.
the alkylene oxides used in the alkoxylation reaction include, in particular, propylene oxide or ethylene oxide or mixtures of these two alkylene oxides. These specifically disclosed alkylene oxides may also be used in succession with each other in the alkoxylation reaction.
Other basically suitable polyols which may be used include those described in, for example, European Patent 380,993, the disclosure of which is herein incorporated by reference.
Suitable blowing agents include water, and other organic blowing agents such as, for example, readily volatile C 1--3 hydrocarbons or organic solvents, such as, for example, acetone or diethyl ether. These other organic blowing agents may be used as blowing agents either individually, or together with water.
the reaction mixtures for the process of the invention may also contain some optional starting components.
These optional components include organic compounds containing at least 2, preferably 2 to 6 isocyanate-reactive hydrogen atoms, and having a molecular weight of 32 to 399.
suitable compounds include diethanolamine, triethanolamine, ethylene glycol, propylene glycol, butane-1,4-diol and the isomers of diethyl tolylenediamine.
These organic compounds are generally present in quantities of 1 to 20% by weight, based on the combined weight of the high molecular weight organic compounds, the blowing agents and/or water, these low molecular weight organic compounds, and the additives.
emulsifiers and foam stabilizers may also be present in the reaction mixtures.
Preferred emulsifiers include, for example, those based on alkoxylated fatty acids and higher alcohols.
Suitable foam stabilizers include, above all, polyether siloxanes, and particularly water-soluble polyether siloxanes. These compounds are generally synthesized in such a way that a copolymer of ethylene oxide and propylene oxide is attached to a polydimethyl siloxane unit.
Foam stabilizers such as these are described in, for example, U.S. Pat. Nos.
the catalysts known per se from polyurethane chemistry such as tertiary amines and/or organometallic compounds, may also be used in the process.
Reaction retarders for example substances showing an acidic reaction, such as hydrochloric acid or organic acid halides
cell regulators known per se such as paraffins or fatty alcohols or dimethyl polysiloxanes and also pigments or dyes, stabilizers against the effects of ageing, plasticizers, fungistatic and bacteriostatic agents and also fillers, such as barium sulfate, kieselguhr, carbon black or whiting, may also be used.
the flameproofing agents used are generally the flameproofing agents known per se, and preferably those products which are liquids at 20° C.
the reaction components are reacted by the one-shot process known per se, by the prepolymer process or by the semiprepolymer process, often using machines, for example, of the type described in U.S. Pat. No. 2,764,565.
the reaction is carded out at an isocyanate index of 50 to 180 and preferably 70 to 120.
isocyanate index also commonly referred to as NCO index
the process according to the invention is suitable for the production of semirigid polyurethane foams (having compressive strength 20 to 400 KPa at 40% compression) with a density of 30 to 500 kg/m 3 and preferably 30 to 200 kg/m 3 , as used in known manner inter alia for the backfoaming of plastic films for the production of film/foam composites for upholstery purposes and for energy-absorbing moldings for the interior of motor vehicles, aircraft, ships and other modes of transportation (instrument panels, interior door linings, armrests, head restraints, side impact protection systems and the like).
Plastic films suitable for this particular purpose are any known surface skins which have hitherto been used in the production of composite film materials by backfoaming of plastic films with polyurethane foams.
surface layers include films of polyvinyl chloride (PVC), polyurethane, polymer blends of PVC and ABS or thermoplastic polyolefins.
the process according to the invention is preferably carded out by lining the inner walls of a mold at least partly with the plastic film to be back-foamed and then filling the mold with the foamable mixture.
Suitable mold materials are metals such as, for example, aluminum, or plastics such as, for example, epoxy resin.
the films used for lining the molds may be formed in known manner by the known technique of thermoforming or the so-called powder-slush technique.
the foamable reaction mixture may be introduced into the mold in such a quantity that the foam formed just fills the mold.
the foams are produced by hand foaming. To this end, all the constituents except for the isocyanate are combined and stirred for 30 seconds (at a speed of 1,000 r.p.m.). The isocyanate component is then added and the mixture is stirred for another 10 seconds at room temperature. In all the Examples, the NCO index is 100.
the flow properties of the reaction mixture were determined in another series of tests in which the polyol formulation, as described below, is reacted with the isocyanate component with stirring at room temperature in a glass beaker.
an OH functional polyester comprising the reaction product of adipic acid/hexane-1,6-diol, and having an OH value 160, 50% solution in butylbenzyl phthalate
the foam was produced in a weight ratio of: 100 parts by weight of polyol formulation a) to 34.4 parts by weight of the isocyanate mixture from Example 1.
the foam was produced in a weight ratio of: 100 parts by weight of the same polyol formulation as in Example 1 and 44 parts by weight of the isocyanate component from Example 2.

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyurethanes Or Polyureas (AREA)
Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

US08/325,715 1993-10-29 1994-10-19 Process for the production of semirigid foams containing urethane groups with improved flow properties Expired - Lifetime US5416125A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4337012.8		1993-10-29
DE4337012A DE4337012A1 (de)	1993-10-29	1993-10-29	Verfahren zur Herstellung halbharter Urethangruppen aufweisender Schaumstoffe mit verbesserten Fließeigenschaften

Publications (1)

Publication Number	Publication Date
US5416125A true US5416125A (en)	1995-05-16

Family

ID=6501378

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US08/325,715 Expired - Lifetime US5416125A (en)	1993-10-29	1994-10-19	Process for the production of semirigid foams containing urethane groups with improved flow properties

Country Status (9)

Country	Link
US (1)	US5416125A (pt)
EP (1)	EP0650993B1 (pt)
JP (1)	JP3655656B2 (pt)
KR (1)	KR100330821B1 (pt)
BR (1)	BR9404264A (pt)
CA (1)	CA2134265C (pt)
CZ (1)	CZ265694A3 (pt)
DE (2)	DE4337012A1 (pt)
ES (1)	ES2126694T3 (pt)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5478866A (en) *	1994-04-27	1995-12-26	Mitsui Toatsu Chemicals, Inc.	Flexible polyurethane foam and process for preparing same
US5491177A (en) *	1994-06-16	1996-02-13	Imperial Chemical Industries Plc	Process for preparing a flexible polyurethane foam
US5674920A (en) *	1994-12-08	1997-10-07	Mitsui Toatsu Chemicals, Inc.	Flexible high resilience polyurethane foam
US5716564A (en) *	1995-01-17	1998-02-10	Bayer Aktiengesellschaft	Process for the production of composite sheet bodies which are suitable as self-supporting components in automobiles
US6096237A (en) *	1997-07-23	2000-08-01	Basf Corporation	Polymeric MDI compositions for use in thermoformable foams
US6210753B1 (en)	1996-08-13	2001-04-03	Fatima Vohs	Process for producing structured coatings made of polyurethane foam
US20090118386A1 (en) *	2006-03-24	2009-05-07	Huntsman International Llc	Process for making a polyurethane foam
US20130244520A1 (en) *	2010-08-16	2013-09-19	Bayer Intellectual Property Gmbh	Fiber composite component and a process for the production thereof

Families Citing this family (4)

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Publication number	Priority date	Publication date	Assignee	Title
DE19632987C1 (de) *	1996-08-13	1998-01-15	Fatima Vohs	Verfahren zum Herstellen strukturierter Beschichtungen aus Polyurethanschaum und Anwendung desselben
US5750583A (en) *	1997-05-28	1998-05-12	Bayer Corporation	Process for the production of molded polyurethane products
DE10220250A1 (de) *	2002-05-06	2003-11-27	Basf Ag	Verfahren zur Herstellung von Pulyurethanhalbhartschaumstoffen
JP2010047635A (ja) *	2008-08-19	2010-03-04	Nippon Polyurethane Ind Co Ltd	軟質ポリウレタンフォーム及びその製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5132334A (en) *	1990-01-20	1992-07-21	Peter Gansen	Polyisocyanate mixtures and their use in the preparation of flexible polyurethane foams

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1993
- 1993-10-29 DE DE4337012A patent/DE4337012A1/de not_active Withdrawn
1994
- 1994-10-17 EP EP94116327A patent/EP0650993B1/de not_active Expired - Lifetime
- 1994-10-17 DE DE59408970T patent/DE59408970D1/de not_active Expired - Lifetime
- 1994-10-17 ES ES94116327T patent/ES2126694T3/es not_active Expired - Lifetime
- 1994-10-19 US US08/325,715 patent/US5416125A/en not_active Expired - Lifetime
- 1994-10-25 CA CA002134265A patent/CA2134265C/en not_active Expired - Fee Related
- 1994-10-27 CZ CZ942656A patent/CZ265694A3/cs unknown
- 1994-10-27 BR BR9404264A patent/BR9404264A/pt not_active IP Right Cessation
- 1994-10-27 JP JP28613494A patent/JP3655656B2/ja not_active Expired - Fee Related
- 1994-10-28 KR KR1019940027863A patent/KR100330821B1/ko not_active Expired - Fee Related

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US5478866A (en) *	1994-04-27	1995-12-26	Mitsui Toatsu Chemicals, Inc.	Flexible polyurethane foam and process for preparing same
US5491177A (en) *	1994-06-16	1996-02-13	Imperial Chemical Industries Plc	Process for preparing a flexible polyurethane foam
US5491176A (en) *	1994-06-16	1996-02-13	Imperial Chemical Industries Plc	Process for preparing flexible foams
US5674920A (en) *	1994-12-08	1997-10-07	Mitsui Toatsu Chemicals, Inc.	Flexible high resilience polyurethane foam
US5716564A (en) *	1995-01-17	1998-02-10	Bayer Aktiengesellschaft	Process for the production of composite sheet bodies which are suitable as self-supporting components in automobiles
US6210753B1 (en)	1996-08-13	2001-04-03	Fatima Vohs	Process for producing structured coatings made of polyurethane foam
US6096237A (en) *	1997-07-23	2000-08-01	Basf Corporation	Polymeric MDI compositions for use in thermoformable foams
US20090118386A1 (en) *	2006-03-24	2009-05-07	Huntsman International Llc	Process for making a polyurethane foam
US8658709B2 (en) *	2006-03-24	2014-02-25	Huntsman International Llc	Process for making a polyurethane foam
US20130244520A1 (en) *	2010-08-16	2013-09-19	Bayer Intellectual Property Gmbh	Fiber composite component and a process for the production thereof
US9808969B2 (en) *	2010-08-16	2017-11-07	Covestro Deutschland Ag	Fiber composite component and a process for the production thereof

Also Published As

Publication number	Publication date
DE4337012A1 (de)	1995-05-04
JP3655656B2 (ja)	2005-06-02
KR950011493A (ko)	1995-05-15
BR9404264A (pt)	1995-07-04
CA2134265A1 (en)	1995-04-30
EP0650993A1 (de)	1995-05-03
CA2134265C (en)	2004-09-07
KR100330821B1 (ko)	2002-11-20
DE59408970D1 (de)	2000-01-05
CZ265694A3 (en)	1995-06-14
ES2126694T3 (es)	1999-04-01
EP0650993B1 (de)	1999-01-13
JPH07188380A (ja)	1995-07-25

Legal Events

Date	Code	Title	Description
1994-10-19	AS	Assignment	Owner name: BAYER AKTIENGESELLSCHAFT KONZERNVERWALTUNG RP, GER Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:ULRICH, LIMAN;GANSEN, PETER;REEL/FRAME:007202/0047;SIGNING DATES FROM 19940907 TO 19940910
1995-05-05	STCF	Information on status: patent grant	Free format text: PATENTED CASE
1997-10-31	FEPP	Fee payment procedure	Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY
1998-10-20	FPAY	Fee payment	Year of fee payment: 4
2002-11-06	FPAY	Fee payment	Year of fee payment: 8
2006-10-25	FPAY	Fee payment	Year of fee payment: 12

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